2-Bromopropionic acid → HCID 54438030, compound

HRID 329211Notes

Reaction equation

HRID 329211 reaction equation
CC(C)([O-])C.[K+].Cl.[CH:8]1([S:14][CH2:15][CH2:16][NH2:17])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.Br[CH:19]([CH3:23])[C:20]([OH:22])=[O:21]>C(O)(C)(C)C>[CH:8]1([S:14][CH2:15][CH2:16][NH:17][C@H:19]([C:20]([OH:22])=[O:21])[CH3:23])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 117292-Bromopropionic acidHCID 214390322-(Cyclohexylsulfanyl)ethan-1-amine--hydrogen chloride (1/1)HCID 23665647Potassium tert-butoxide

Product 1

HCID 54438030HCID 54438030, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a stirred solution of 22.4 parts potassium tert-butoxide in 400 parts by volume of tert-butanol, under a nitrogen atmosphere, is added successively 19.62 parts of 2-(cyclohexylthio)ethylamine hydrochloride and 15.3 parts of 2-bromopropionic acid. The mixture is refluxed for 3 hours, then dried under reduced pressure. The material remaining is dissolved in 200 parts of water containing 10 parts of sodium hydroxide and extracted with ether. The aqueous solution is cooled in an ice bath and acidified to pH 5 with concentrated hydrochloric acid. The solid is collected by filtration and dried under reduced pressure to yield N-[2-(cyclohexylthio)ethyl] alanine.

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. customdried under reduced pressure
  3. dissolutionThe material remaining is dissolved in 200 parts of water containing 10 parts of sodium hydroxide
  4. extractionextracted with ether
  5. temperatureThe aqueous solution is cooled in an ice bath
  6. filtrationThe solid is collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-198cea847a4044c5b5e07715f694a620
Source dataset
uspto-grants-1977_04
Patent number
US04020079

Reaction notes

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